Buchwald–Hartwig amination: Ethyl 4-bromobenzofuran-2-carboxylate → Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate
0% yield, run at 50 °C, as recorded by experimental reaction archive. The written procedure is below. One of 3 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Ethyl 4-bromobenzofuran-2-carboxylate | C₁₁H₉BrO₃ | |
| Reactant | 1-Benzylpiperazine | C₁₁H₁₆N₂ | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate | C₂₂H₂₄N₂O₃ | 0% |
Conditions
- Temperature
- 50 °C
Yield
- 0% of Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate.
Every recorded run making this product
3 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl; Bis(dibenzylideneacetone)palladium | Cesium carbonate | 1,4-Dioxane | 95 °C | — | 27% |
| 2-(Di-tert-butylphosphino)biphenyl; Bis(dibenzylideneacetone)palladium | Cesium carbonate | Toluene | 100 °C | — | 0% |
| Binap, (A+-)-; Bis(dibenzylideneacetone)palladium | potassium 2-methylpropan-2-olate | Toluene | 50 °C | — | 0% (this run) |
Procedure
Copied from the source record, unedited
**Purpose:** Buchwald-Hartwig coupling using unpurified ethyl 4-bromobenzofuran-2-carboxylate. The analysis on crude 4-bromobenzofuran-2-carboxylate shows traces of non cyclized and non aromoatized by-products. 2010-03-02 15:25:22: To a 25 mL roundbottomed flask was added ethyl 4-bromobenzofuran-2-carboxylate (LR; 1 g; 3.72 mmol) and toluene (7 mL/g-bulk- LR; 7 mL). The mixture was concentrated under reduced pressure. To the mixture was added toluene (7 mL/g-bulk-LR; 7 mL) and the mixture was concentrated a second time under reduced pressure. To the mixture was added toluene (7 mL/g-bulk-LR; 7 mL) followed by 1-benzylpiperazine (1.3 eq; 0.852 g; 0.84 mL), BINAP (0.04 eq; 93 mg) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.02 eq; 68 mg). The mixture was stirred for 5 minutes followed b
The source
This record comes from experimental reaction archive (ord-724091f002d04d2ea6bfe923f45ebf01). Open the source and check it against what is on this page.
experimental reaction archive record ord-724091f002d04d2ea6bfe923f45ebf01 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
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Where to next
More Buchwald–Hartwig amination records
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